Fluorescent compound, method for producing the same, and fluorescent resin composition

Abstract

The present invention provides a fluorescent compound represented by the following general formula (1): wherein R 1 to R 4 each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, halogen atom, hydrogen atom, amino group, cyano group, amine-containing group, and siloxane-containing group; with the proviso that when an amine-containing group as the substituent is not included, at least one of R 1 to R 4 is a siloxane-containing group represented by S x -A-, and that when an amine-containing group as the substituent is included, at least one of R 1 to R 4 and a substituent of the amine-containing group is a siloxane-containing group represented by S x -A-; a method of producing the same; and a fluorescent resin composition containing the same.

What is claimed is: 
     
       1. A fluorescent compound represented by the following general formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1  to R 4  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a hydrogen atom, an amino group, a cyano group, an amine-containing group represented by the following general formula (2), and a siloxane-containing group represented by the following general formula (3); or the carbon atoms at the ortho position of the nitrogen atom bonded to X directly bond to each other to form a carbazole ring structure, resulting in that R 1  is not present; 
         with the proviso that when an amine-containing group represented by the general formula (2) as the substituent is not included, at least one of R 1  to R 4  is a siloxane-containing group represented by the following general formula (3), and that when an amine-containing group represented by the following general formula (2) as the substituent is included, at least one of R 1  to R 6  is a siloxane-containing group represented by the following general formula (3), 
         each of X may be identical or different, represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms, and some of the carbon atoms may be substituted with a heteroatom; and
 n is an integer of 0 to 5: 
 
       
       
         
           
           
               
               
           
         
         wherein R 5  and R 6  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, halogen atom, hydrogen atom, amino group, and siloxane-containing group represented by the following general formula (3); and 
         m is 0 or 1;
   S x -A-  (3)
 
 
         wherein S x  represents a linear, branched or cyclic organosiloxanyl group having 2 to 10 silicon atoms and a monovalent hydrocarbon group having 1 to 20 carbon atoms bonded to at least one of the silicon atoms; and 
         A represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms which may contain at least one of —S— or —NR 0 —, or a combination thereof, with the proviso that heteroatoms of sulfur and nitrogen are not adjacent to each other except the case where A is a cyclic divalent hydrocarbon group, and R 0  is a monovalent hydrocarbon group having 1 to 20 carbon atoms. 
       
     
     
       2. A fluorescent compound represented by the following general formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1  to R 4  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a hydrogen atom, an amino group, a cyano group, an amine-containing group represented by the following general formula (2), and a siloxane-containing group represented by the following general formula (3); or the carbon atoms at the ortho position of the nitrogen atom bonded to X directly bond to each other to form a carbazole ring structure, resulting in that R 1  is not present; 
         with the proviso that when an amine-containing group represented by the general formula (2) as the substituent is not included, at least one of R to R 4  is a siloxane-containing group represented by the following general formula (3), and that when an amine-containing group represented by the following general formula (2) as the substituent is included, at least one of R 1  to R 6  is a siloxane-containing group represented by the following general formula (3); 
         each of X may be identical or different, represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms, and some of the carbon atoms may be substituted with a heteroatom; and 
         n is an integer of 0 to 5: 
       
       
         
           
           
               
               
           
         
         wherein R 5  and R 6  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, halogen atom, hydrogen atom, amino group, and siloxane-containing group represented by the following general formula (3); and 
         m is 0 or 1;
   S x -A-  (3)
 
 
         wherein S x  represents a linear, branched or cyclic organosiloxanyl group having 2 to 10 silicon atoms and a monovalent hydrocarbon group having 1 to 20 carbon atoms bonded to at least one of the silicon atoms; and 
         A represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms which may contain at least one of —O—, —S— or —NR 0 —, or a combination thereof, with the proviso that heteroatoms of oxygen, sulfur and nitrogen are not adjacent to each other except the case where A is a cyclic divalent hydrocarbon group, and R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, 
         and wherein, in the general formula (1), n is 1, 3, or 5, and at least one of R 4  is a siloxane-containing group represented by the general formula (3). 
       
     
     
       3. A fluorescent compound, represented by the following general formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1  to R 4  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a halogen atom, a hydrogen atom, an amino group, a cyano group, an amine-containing group represented by the following general formula (2), and a siloxane-containing group represented by the following general formula (3); or the carbon atoms at the ortho position of the nitrogen atom bonded to X directly bond to each other to form a carbazole ring structure, resulting in that R 1  is not present: 
         with the proviso that when an amine-containing group represented by the general formula (2) as the substituent is not included, at least one of R 1  to R 4  is a siloxane-containing represented by the following general formula (3), and that when an amine-containing group represented by the following general formula (2) as the substituent is included at least one of R 1  to R 6  is a siloxane-containing group represented by the following general formula (3); 
         each of X may be identical or different, represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms, and some of the carbon atoms may be substituted with a heteroatom; and 
         n is an integer of 0 to 5: 
       
       
         
           
           
               
               
           
         
         wherein R 5  and R 6  each independently represent a substituent selected from a linear, branched or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, halogen atom, hydrogen atom, amino group, and siloxane-containing group represented by the following general formula (3); and 
         m is 0 or 1:
   S x -A-  (3)
 
 
         wherein S x  represents a linear, branched or cyclic or organosiloxanyl group having 2 to 10 silicon atoms and a monovalent hydrocarbon group having 1 to 20 carbon atoms bonded to at least one of the silicon atoms; and 
         A represents a single bond, or a linear, branched or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms which may contain at least one of —O—, —S— or —NR 0 —, or a combination thereof, with the proviso that heteroatoms of oxygen, sulfur and nitrogen are not adjacent to each other except the case where A is a cyclic divalent hydrocarbon group, and R 0  is a monovalent hydrocarbon group having 1 to 20 carbon atoms, 
         and wherein, in the general formula (1), at least one of R 2  is an amine-containing group represented by the general formula (2), and at least one of R 5  is a siloxane-containing group represented by the general formula (3). 
       
     
     
       4. The fluorescent compound according to  claim 1 , wherein, in the general formula (1), n is 0, and at least one of R 2  is a siloxane-containing group represented by the general formula (3). 
     
     
       5. A fluorescent resin composition comprising the fluorescent compound according to  claim 1  and a resin. 
     
     
       6. The fluorescent resin composition according to  claim 5 , wherein the resin is a silicone resin. 
     
     
       7. A method for producing a fluorescent compound according to  claim 2 , comprising a step of reacting an amine compound represented by the following general formula (4) with an aromatic halogen compound represented by the following general formula (5) in the presence of a transition metal catalyst: 
       
         
           
           
               
               
           
         
         wherein R 4a  is identical to R 4  in the general formula (1); 
       
       
         
           
           
               
               
           
         
         wherein R 1a  to R 4a  are identical to R 1  to R 4  in the general formula (1), respectively; 
         Z a  is a halogen atom; 
         X a  is identical to X in the general formula (1); and 
         o represents an integer of 0 to 2, and satisfies, together with n in the general formula (1), o=(n−1)/2. 
       
     
     
       8. A method for producing a fluorescent compound according to  claim 3 , comprising a step of reacting an amine compound represented by the following general formula (6) with an aromatic halogen compound represented by the following general formula (7) in the presence of a transition metal catalyst: 
       
         
           
           
               
               
           
         
         wherein R 5b  is identical to R 5  in the general formula (2); 
       
       
         
           
           
               
               
           
         
         wherein R 1b  to R 4b  are identical to R 1  to R 4  in the general formula (1), respectively; 
         X b  is identical to X in the general formula (1); and 
         n b  is identical to n in the general formula (1), with the proviso that at least one of R 2b  represents a substituent represented by the general formula (8); 
       
       
         
           
           
               
               
           
         
         wherein R 6b  is identical to R 6  in the general formula (2); 
         m b  is identical to m in the general formula (2); and 
         Z b  is a halogen atom. 
       
     
     
       9. A method for producing a fluorescent compound according to  claim 4 , comprising a step of reacting an amine compound represented by the following general formula (10) with an aromatic halogen compound represented by the following general formula (9) in the presence of a transition metal catalyst:
   Z c —X c —X c —Z c   (9)
 
 wherein X c  is identical to X in the general formula (1); and 
 Z is a halogen atom; 
 
       
         
           
           
               
               
           
         
         wherein R 1c  and R 2c  are identical to R 1  and R 2  in the general formula (1), respectively. 
       
     
     
       10. A fluorescent resin composition comprising the fluorescent compound according to  claim 2  and a resin. 
     
     
       11. The fluorescent resin composition according to  claim 10 , wherein the resin is a silicone resin. 
     
     
       12. A fluorescent resin composition comprising the fluorescent compound according to  claim 3  and a resin. 
     
     
       13. The fluorescent resin composition according to  claim 12 , wherein the resin is a silicone resin. 
     
     
       14. A fluorescent resin composition comprising the fluorescent compound according to  claim 4  and a resin. 
     
     
       15. The fluorescent resin composition according to  claim 14 , wherein the resin is a silicone resin.